Teen Dragon
by Prince Yarar
Summary: Hiccup was the son of Berk's Police Chief who accidentally became a gang leader. Toothless was his bodyguard/mentor/big brother figure who perhaps liked sushi a little too much. Astrid was Hiccup's exasperated girlfriend/second-in-command. It was all fun and Robin Hood styled crimes until Jack Frost, the heir to a powerful Family decided to strike a deal with him.
1. Chapter 1

**AN: **To understand the story better, I would suggest you go to my tumblr (yarrayora) and search the tag 'teen dragon'. Because this story takes place quite some time after Hiccup became a gang leader. I'm just too lazy to write a proper chapter explaining Hiccup's fortunate accident of being a mob boss.

* * *

"Hiccup, I don't like that guy…" Toothless complained to his leader and best friend. "Why can't I drown him?" He was referring to Fucking Jack Frost, the smug guy they met earlier.

Hiccup gave a long suffering sigh before whispering back to Toothless. "Do you even know who that guy is? That's Jack Frost, only son of Nicholas Frost the don of a particularly large and fearsome mob. Nicholas loves his son to death and if so much as one hair gets harmed on his head it could mean trouble for all of us." Hiccup explained "Look I know it's hard but we have to play nice if we want to get on his and his dad's good side so please behave and I'll get you sushi afterwards"

Toothless grumbled. Hiccup had a point, he always do. And the lure of sushi was too much for him to disagree. That was why Hiccup was the leader. "Fine…"

"But I still can fantasize drowning his bleeding body."

"Hush" Hiccup sighed a half smile showing that he wasn't as annoyed as he pretended to be. "He's not that bad, he's certainly not the first to underestimate me either. I'd rather be underestimated than overestimated" He looked down at his watch "We have a group meeting in half an hour, we better hurry"

Toothless smirked. Of course, he knew that. Underestimating Hiccup was the reason why his name was Toothless now. He didn't regret it tho, because in return they gained a cunning leader with a connection to the police. And Fucking Jack Frost wouldn't even see the wrench coming. "Yes sir."

* * *

The meeting (or if it could even be called that, it was more like an informal gathering of whoever could make it at the time,) was a very simple one. They talked about any trespassers from rival gangs that crossed into Dragon Territory, and how the mayor swore she would crack down on the recent crime spree with the help of Chief of Police AKA Hiccup's dad. "If he ever finds out I'm so dead" Hiccup sighed checking his watch every few minutes, "I've been meaning to ask, where do you all live?" He asked his attentive subordinates.

Huh, come to think of it, they never _did_ tell him about their circumstances. The twins shuffled uncomfortably beside him before Toothless decided to answer for them. "Most of us are either a runaway or got kicked from our own house. We live here, in the warehouse. Of course we sometimes switch places to confuse the police, but you get the idea." He ended with a shrug.

Hiccup couldn't help but feel concerned for their situation. Not only because they were is gang but more because they were his friends. This warehouse was cold and not very well lit, meanwhile Hiccup had a warm bed to go home to every night and that just wasn't fair. But what could he do...he couldn't exactly bring them all home with him. I mean that would be a talk that went over well 'Hey dad, that gang you've been hunting, they've named me their leader and by the way can the stay here?' "I'm sorry, it must be difficult for you all. I wish I could do more to help..."

"Same..." Astrid agreed, her face sad.

The Dragons couldn't help but to stare. They were so used with people condemning them or even ignoring that they existed. So it was a weird but not an unwelcome change to hear a sincere wish to help them. "Thank you..." Hookfang blushed and smiled at Hiccup. No one understood why one of their femme fatale always turn to a schoolgirl around their leader. Toothless rolled his eyes at her before turning to Hiccup. "S'fine, we always get by." he then added, "Of course, you buying us sushi helped a lot."

Stormfly groaned loudly, "You and your fucking sushi... I want to eat real meat once in awhile."

"Sushi IS a real meat you bitch!" Toothless snarled.

Astrid rolled her eyes at the idea of another fight breaking out, though by now she was used to it. If things got dangerous she and Hiccup would break it up, but for now, let them let out some energy. In the far corner of the room she noticed a person dressed in ripped jeans and a metal band t-shirt that she had never seen before today. As subtly as possible she nudged Hiccup's side and tilted her head towards the man. "He look familiar to you?"

Hiccup turned in the direction she indicated, his eyes widening slightly when he realized that he did recognized him. "Unfortunately yes...that's one of my dad's new trainees." Hiccup gasped sort of backing away. It didn't seem like the guy noticed him yet. But what to do, if he told Toothless and the others they would kill him, and the guy was so nice to Hiccup at the station. On the other hand he couldn't let him get away and report to his dad, that would be even worse for everyone.

* * *

Anderson, to be honest, was surprised by how easy it was to infiltrate The Dragon. He expected something more challenging, but he wouldn't look at a gift horse on his teeth... Or whatever the saying went. The meeting was rowdy and he wasn't sure which one was the dangerous Night Fury, no one ever saw him or lived long enough to give a description. There was one guy that he thought to be the infamous leader, but the lack of respect and his nickname 'Toothless' made him think otherwise. So he stayed in the shadow, watching and observing. There was two kids that dressed differently than the others. New recruits perhaps? Their clothes did looked nicer and newer than the rest of the group. When the meeting started, he couldn't help but to think he had saw the boy in the Daddy Dragon t-shirt before. But where?

* * *

"What are we going to do Hiccup?" Astrid whispered keeping her gaze away from the man while keeping him in her peripherals. "If he reports to your father you will be disowned and we'll be screwed."

"I know I'm thinking!" Hiccup hissed trying to silently signal Toothless "I may have to disappear."

Toothless, for his credit, was still keeping an eye on his leader even while kicking Stormfly's butt. Wasn't even hard to do with the punk being weaker than him. Toothless blinked his eyes several times in response, something that they had practiced to give a quiet message. "I'll make a distraction." was signaled. Since he already did start a fight with Stormfly, escalating it a few level wouldn't hurt. In fact, she might even appreciate the new scars he was about to make. Toothless flipped his knife out, the one that made him famous as The Night Fury. "Come on bitch, can't be tired already can you?"

Stormfly snorted, but she noticed a play when she saw it. "Bring it, Toothie."

Hiccup caught the signal right away and he and Astrid backed out slowly hoping the cop didn't notice them. They took the back exit, running through the alleyway and climbing the chain link fence."Wait we can't just go!" Astrid piped in catching Hiccup by the arm. "They don't know that the guy is a cop we have to warn them!"

"How are we going to warn them without giving away who we are?" Hiccup huffed. "The best I can do is destroy the info he's gathered at the police station...that's if he doesn't recognize me..."

"We have the element of surprise" Astrid smiled slightly picking up a PVC pipe and swinging it a few times experimentally."This whole gang thing has been a terrible influence on you..." Hiccup said with a half smile following after her.

* * *

Anderson ducked another chair that was thrown to his direction. The fight between Toothless and Stormfly somehow evolved into a full blown war, with people taking sides between the two. This was insane! How could a rowdy gang like this hadn't been caught yet?! They were so loud and disorganized, unlike the impression he got from the briefing. Either this was all a giant hoax or their leader was so scary good at what he was doing. Another thrown bottle and Anderson was sure that he should leave immediately. The meeting was over, he won't get anything else. Slowly he creeped outside and sighed in relief when he thought he was finally safe, lowering his defenses.

Later he would regret it when he woke up in the hospital. His head felt like it would split when he touched it. The Chief was there, looking angry and disappointed. "How did they found out?"

"I don't know sir..." Anderson hung his head in shame. "I did thought it was too easy... They didn't even glance at me." The rookie tilted his head slightly, "What about the hidden camera?" He asked, hopefully there was something that could be salvaged.

Stoick shook his head grimly. "They searched you thoroughly before dropping you near my house..." there was rage dripping from that sentence, "Hiccup found you and called me after trying to stop the bleeding from your head." The man closed his eyes, and Anderson couldn't even begin to think about how The Chief felt right now.

The Dragons not only found out about their plan, but they also taunted them. And The Chief's son was home alone when it all happened, vulnerable to the attack that might befall him. "Is your son okay, sir?"

"He's fine, shaken but fine. He did well with the first aid, you should thank him when he comes." Anderson could hear the recognition in Stoick's voice. It made him smile a little. Hiccup was a good kid, and it was about time The Chief saw it too.

"Of course sir."

* * *

Of course Hiccup wasn't going to go visit Anderson. God forbid he recognized him. He played his part well enough, asked how Anderson was doing when his dad got home, faked concern when his dad told him all the evidence was gone."I really can't go dad I got a lot of homework this week...as long as he's ok that's all I need to know."

His dad agreed, before telling Hiccup that he would be working another late shift tonight. Giving him the whole thing about locking the door, not going out after dark...ect."I'm proud of you son, you handled things very well. You're growing up to be quite the young man" Stoick said clapping Hiccup on the shoulder with his beefy hand.

"Yeah...thanks dad..." Hiccup tried to smile even though he felt like a knife was twisting in his gut.

Once his dad left the house for work, he waited a bit before leaving the house out the back way and locking the door behind him. Sure enough, Toothless was there waiting."So what have we learned from this whole heart attack inducing ordeal about new membership?" Hiccup being only half sarcastic, he was still feeling like shit for lying to his dad.

"That we are being too accepting and you should buy me sushi while giving a lecture?" He was expecting a glare, but Hiccup looked too tired to even give a snark. Toothless' expression soften. The boy could just have refused his position and tell his dad everything from the start. But he didn't, he lied and he tricked others to help The Dragons, because he saw them as who they were, not a group of troublemakers, not The Night Fury, just them. A bunch of kids huddled in a warehouse because no one else would care.

"Look." Toothless grabbed Hiccup's shoulders and looked at him in the eyes. "I did this, I dragged you into this whole mess. I would say I'm sorry, but I'm not. I'm glad I have met you, and dammit Hiccup, if this made you feel like a little shit then I- no, _we_ would do everything we can to make you feel better." He wasn't sure if he was making any sense. He just spew what he felt and he wasn't really good with this whole touchy feeling things. "So yeah, just tell us what to do, and we will follow." Toothless let go. "We trust you."

Hiccup blinked owlishly before smiling, leave it to Toothless to remind him why he was doing this whole thing in the first place."Thanks, Toothless" He reached up lightly giving Toothless a pat on the head. He knew it was hard for Toothless to express feelings in a way that wasn't condescending or sarcastic, the fact that he was trying made Hiccup feel a lot better about lying."I'm glad you feel that way...because in about five minutes you are going to be pissed and probably hate me." Hiccup chuckled lightly, shoving his hands into his pockets, "You are never going to guess who invited us out for sushi this evening?"

**Hint: **It's Fucking Jack Frost


	2. Chapter 2

He was torn. Toothless couldn't decide if he hated Fucking Jack Frost more than he loved sushi. Wait, that was a lie, he wouldn't refuse sushi for anything (except if it involved Hiccup). So there they were, sitting on their seat in a fancy sushi restaurant that Toothless always wanted to visit. Him and Hiccup looked out of place with their casual clothing, but Toothless didn't really care. He was here for food, not to impress onlookers.

He eyed the place, finding several exits and hidden bodyguards all over the place. And trap exits. Oooh, this Jack Frost was good. The brat smiled widely at them. "Glad you can come! I would have thought you would be too busy with your father!" Toothless tensed, did he know about Stoick? "Oh, don't look so surprised. Of course we know! We keep tab on every up and rising newcomers." He winked. It made Toothless angrier, because it wasn't too long ago Fucking Jack Frost told Hiccup he didn't look like much.

"You are the son of the Police Chief, yes? I've read your school profile and you don't look like much. But you are so much more than that, right?" Fucking Jack Frost leaned closer. "You even tamed The Night Fury." Toothless was about to strangle the brat when he felt Hiccup's hand on his shoulder, he reluctantly sat back down. Fucking Jack Frost looked absolutely delighted. "See? You keep him on a leash!"

Hiccup could feel Toothless' anger without even looking at him and kept a steadying hand on his shoulder. Since their first meeting Hiccup had made it a point to do his research about Jack and his dad using his father's police records and whatever he could get from Gobber had one beer too many.

Jack was maybe a year or two older and since there were no school records Hiccup could assume that his family was either extremely secretive or Jack was home schooled, either was a possibility. They were successful, if the restaurant and the way Jack dressed was anything to go by, and Jack's little habit of asking questions he seemed to know the answers to was an obvious ploy for some sort of reaction, either attention or amusement. Either way, Hiccup decided he wasn't going to give it to him, and put on his best poker face. If this was just a game to Jack then Hiccup was more than willing to play.

"Since you clearly already know everything about me and The Night Fury..." He used the old name seeing as how the new name would only get a laugh out of Jack, which was not the desired reaction. "Perhaps I could ask a few questions instead, a nice little ice breaker perhaps, like why you wished to speak with us."

Jack looked amused. "Well, maybe..." He purred, "Maybe I just want to see you." His hand was reaching slowly to touch Hiccup's hair.

Toothless reacted quickly and grabbed the brat's hand by its wrist, which resulted in the not-so-hidden bodyguards standing by with their guns. Fucking Jack Frost smiled at him, and Toothless snarled. "Don't touch him."

Jack raised his other hand, signaling his subordinates to calm down. They lowered their guns hesitantly. "So, tell me Mr. Night Fury." God, this brat was worse than Stormfly, "Why him?" He gestured to Hiccup.

"You didn't even fucking answered his question." Toothless gripped his wrist tighter, silently cheered in victory when Jack winced."Pretty sure I did. I just said that I wanted to see him.""Don't give me that fake innocent face." In his mind, Toothless added, 'who the fuck do you think invented it?'"Oh yeah, you got me." Fucking Jack Frost rolled his eyes. "I'm just curious. Of all people that could be your new leader, why him? You are not the type of person who would give up your title just by asking you nicely." He shrugged. "So, why him?"

Toothless narrowed his eyes in suspicion. What was he trying to say? He wanted to know why Hiccup was the leader? "And can you let me go? Because I think you just stopped the blood flow in my wrist." The former Night Fury glanced at Hiccup, who nodded. Toothless let go and Jack shook his hand experimentally. "And there it was again." The Frost Heir said. "You asked for his permission before doing anything. You see, my Family had been watching you closely for a long time. You had never done that before." He pursed his lips. "What's so special about him?"

The Dragon blinked.

Oh. Oh! This was rich! Toothless let out his infamous breathy laughter, which spooked the bodyguards. Jack looked at him bemusedly. "What's so funny?"

"Is the Heir of the Frost Family... are you_ jealous_?" Toothless let out another round of laughter when Jack spluttered. "You _are_!"

Hiccup lightly rolled his eyes at Toothless' display of glee having fallen off his chair and rolling on the floor. Much to his surprise Jack's face had turned a bright red from his nose to the tip of his ears, as he weakly stuttered out protests. "N-no I'm not-! Why would I-?!" Homeschooled it was. Which wasn't that unusual, most Heirs to larger, powerful families were. Hiccup had no doubt in his mind that maybe Jack just didn't know how to speak to people his own age, he was maybe even a little bit lonely.

"I don't really see what you have to be jealous about Jack." Hiccup smiled intertwining his hands and resting his chin on the laced fingers. "You have just _so_ many loyal subordinates who follow your every whim and see to your safety. The friendship me and The Night Fury have must seem... rather trivial to someone as great and powerful as you." Hiccup gently nudged Toothless with his foot indicating that he should probably stop laughing and get up before he got himself a food cramp from laughing too hard."As for how I became leader and why, that is really none of your business. I don't ask about your family or your family's inner structure. To do that would be just plain rude after you kindly treated us to this lovely dinner."

"If that is all? We really must be going, see I was under the impression you were going to call us here about something important, like what I knew about Pitch Black or perhaps even a possible alliance. But clearly I was wrong, you just wanted to play games." Hiccup spoke nonchalantly giving a slight shrug as he got up from the table and turned away. "Let's go Night Fury this was a waste of time."Hiccup turned away with Toothless in tow heading towards one of the exits while doing a countdown in his head. After all the idea was planted and it would come to fruition in

3...

2...

"Ugh, fine, let's talk business." Jack said unhappily and Toothless needed to hold back his laughter. Oh boy, what a kid. Stopping in place for a few moment (to give an impression that they were thinking) they got back to their seat in front of a bemused Jack Frost. Well, this turned out to be fun. Jack spreaded his arms, "So." He said, "We know about your skirmishes with your Mayor, and you know about our skirmishes with my lovely uncle Pitch." He smiled bitterly. "The question is, what are we going to do about it?" Toothless almost roll his eyes. Sheesh, what a Diva. "Of course, we could try the usual boring stuff, like criss-cross." Jack put his chin on his hand, while his other hand was stirring his straw. "But that's not what I want... and I'm sure that's not what you want." He looked at Toothless dead in the eyes, "You want revenge, I want revenge. Just taking them down wouldn't be enough."

The dark haired man return the gaze with the same intensity. The brat knew. "Your mayor hides behind the crusade of justice while my uncle hides beneath the shadows. We can lure them out, and everything else will be easy. We just have to find the bait." Jack leaned on his chair. "I have yours."

Toothless gripped his chair tightly. He knew, he knew, he fucking knew and had it. The fucking document they had been searching for months."You know who her son is?" The man growled.

"No, not really." Jack waved his hand dismissively, "We only had the proof that she abandoned her son. It doesn't mean we can't make her think we have more." The platinum blonde smirked. "I'll give it to you if you can find Pitch for me."

Hiccup pondered over the offer, if it was too good to be true there had to be a catch. Pitch wasn't an easy man to find, he worked for public officials and mob bosses as a professional hit man for hire. He had an idea about how to draw him out but if anything went wrong it could mean trouble for The Dragons. Maybe there was a way he could solve two problems with one solution but he still wasn't too sure yet if Jack could be trusted. He needed to pull more emotion out of him, push his buttons find out what made him angry, and vulnerable. He had a little tidbit of info he had gathered from extensive research and wondered if maybe it would be a tender enough subject to piss him off.

"A question, before I agree or disagree to your terms." Hiccup said his arms folded over his chest as he leaned back. "You said 'For me' so I have to wonder... does your dad know about this exchange?" He narrowed his eyes and speaking softly for no other purpose than to make Jack listen. "If he is even your real father."

There was a hard gleam on Jack's eyes. His fake easy going smile was turning predatory. Toothless knew that look. He knew because he used that expression often. Jack was angry, but there was something else. The brat wanted to make Hiccup fell, hard and painful. The bodyguards looked uneasy and edged away from their charge, as if afraid they would get hurt. "I will be honest with you." His expression changed so quickly it was almost unnoticeable. "My father doesn't know about our meeting, and it's very likely I will get punished if he finds out." He slurped his drink with his straw. "You know, a bit like your situation with your own dad."

Oh, he was really going to go there.

"I know how hard it feels to lie to your own father, like a little shit, yea? Especially when he disapprove what I was doing, even though it was for his own good." The heir smiled wistfully, it was hard to know whether or not he was being sincere. Toothless glanced at Hiccup, waiting for his reaction.

Hiccup sucked in air through his teeth, feeling the sting in the words as well as the rage rolling off to boy in front of him. He supposed he deserved the jab at his rocky relationship with his father for being cruel. But he at least had his answer and at the very least he could trust Jack to keep his end of the deal.

"I'm sorry for making assumptions, I was wrong, clearly you are very much his son" Hiccup sipped lightly at his drink, ignoring his bully induced gut reaction to stand up and make a break for the door. "Not by blood but definitely in the way that counts. He probably doesn't want you involved in his business because it's dangerous. He wants to protect you too."

Hiccup glanced to the side at Toothless before focusing his attention back on Jack.

"I have plan to draw Pitch out...but I'm going to need a few small things on your part." Hiccup said with a shy smile. "If you even still want to work with us that is. I'm worried I might have gone a little too far with pushing your buttons."

Jack shrugged, "Eh, I have heard worse." Toothless thought he saw a genuine smile from the boy, but it left as quickly as it appeared. "Ask and ye shall receive." Alright, that did it, Jack Motherfucking Frost was a full time Diva.

Hiccup smiled, happy some of the tension melted and that Jack was back to his usual punchable self. "Ok first thing, we need a new base. A safe house, preferably with running water and heating. Location doesn't matter but it would be nice if it were somewhere out of the way. Plan on it fitting at most about 30 people who are perfectly happy sleeping wherever there is room. Furnishing is optional."

"Now if you just want us to_ find_ Pitch that will be easy to draw him out but would you rather we lure him to a designated location? Perhaps a location where you will have some of your men waiting?" Hiccup asked, wondering just how deep Jack's desire for revenge went.

Jack's mouth twitched at the word 'his men'. Oh no, he rather do the deed himself. "No need for a specific place. Just lure him to my town, or yours... actually I don't care which town he is going to die in. But I expect a report for each time you managed to find him, in exchange, I would give you a safe house..." He snapped his finger and one of his underlings gave him a map of Berk. "Let's see, we have two available here and here." He pointed, one in the forest near Hiccup's school, and another near the dock. "You can use both, easier for access that way. My men will clean it up a bit and it will be ready to use in... say, three days?"

"Three days sounds good" Hiccup nodded shifting slightly. What could Pitch have done to anger Jack so much as to make him want to kill Pitch? Hiccup was uncomfortable at the idea of killing, it didn't matter whether the person deserved it or not. But if this is what it took to get them a proper home and evidence towards taking down that witch of a mayor...it would be a small price for him to pay.

He wondered if it would be worth it in the end for Jack too."I just need a way to contact you quickly. maybe your number. If you don't mind, I may also give your number to my second in command and Toothless so if in the event of something going wrong, you'll get the reports."

"Toothless?" Jack looked amused. "I'm going to take a shot in the dark and assume that Toothless is our dear Night Fury here." Toothless bit back a snarl when he saw the laughter in Jack's eyes.

"You don't have the right to call me Toothless." He huffed.

"Why not?"

"I don't like you." Of course, he also didn't like Stormfly, but she was also a Dragon, so he let it slide.

The brat chuckled, "Big surprise there."

"Really? I thought I was obvious enough." Toothless deadpanned.

Hiccup couldn't believe he had let the nickname slip out, he had dropped his guard around the Mafia Heir forgetting for a minute that they were just business partners, not really friends."Sorry..." Hiccup said awkwardly reaching up to run a hand through his hair. "Toothless is more of a nickname his friends give him and you aren't really..." He let the sentence sort of hang there not really sure how to continue. Maybe he should just shake his hand and leave before he made an even bigger idiot of himself.

Jack stared at Hiccup's hand for awhile before shaking it. "It was a pleasure meeting you, Hiccup." He then turned his head slightly to Toothless. "And you too, Mr._ Night Fury_." he put an emphasis on his street name, which made Toothless wanted to run a knife through his heart. God, what a little shit."Come on Hic, it's getting late, your dad would be home soon." The dark haired man grabbed his friend and dragged him outside. He ignored Jack, who was waving goodbye at them.

Once they were outside, Toothless let Hiccup go and let out a frustrated angry groan which he surpressed ever since he met Jack. "The sushi was good, but Fucking Jack Frost ruined my appetite." He then started his motorcycle, eager to leave. "I will never visit Burgess again."

Hiccup rolled his eyes getting on behind him. "It wasn't so bad. We got you guys a better base out of it. One with heating and running water." Hiccup sighed holding out a helmet to Toothless. "I know you hate it but at least put it on for me." He sighed putting his own helmet on.

Toothless wore his helmet with a scowl. "Well, okay, it's not_ that_ bad. I got to laugh at him." He chuckled with that weird 'heh heh heh' noise of his. He couldn't see Hiccup's face under the helmet, but he was pretty sure the teen just rolled his eyes again. "Ready to go home?"

* * *

The ride home was easy enough. Hiccup was getting used to the gut lurching feeling being on a vehicle with no real barrier between himself and the outside. Better than when he first started out. He took a minute to ponder over his plan he would need to discuss it with Toothless once they got their base.

Once they arrived to the house they noticed his dad was home, his police cruiser parked in the driveway along with another, unfamiliar car."Shit!" Hiccup cursed "Back way! Back way!"

Toothless made an abrupt turn, almost throwing both of them off the motorcycle. He grinned at the rush of adrenaline he was getting. Although this was not the time to be distracted. The Chief was home, and if he found out Hiccup wasn't there, it could mean trouble. He stopped his bike in the nearest alley behind Hiccup's house. Toothless didn't take off his helmet in case someone recognized him. Which was dubious because no one outside his gang (and Fucking Jack Frost with his Family) knew who The Night Fury was. But better be safe than sorry.

Hiccup had no idea who the other car belonged to but he hoped that it was someone who could keep his dad distracted while he slipped into the window. Hiccup removed his helmet before waving Toothless off. "I'll call you if something goes wrong, get out of here before you get caught!" With that said he climbed up the trellis that they used for ivy vines to the roof and from there, after checking to see if the coast was clear, he slipped in grabbing some textbook so as to pretend he was reading just as his dad walked in."Oh son! You were so quiet up here" Stoick laughed giving his son a firm pat on the shoulder."Haha well you know me" Hiccup smiled shakily. That was close..."Come downstairs there is someone I want you to meet" Stoick's grip on his shoulder left no room for argument as he led the boy downstairs.

Sitting there in The Haddock's living room was Pitch Black, sipping on his coffee like the house was his own. He put the cup down when The Chief came down with his son. He gave the boy his winning smile, which somehow only served to make him tense. Huh, it seemed this boy knew his reputation. "Hello there, you must be Hiccup."

Hiccup heart shot into his throat. Of course, of course Pitch would be there sitting in his living room, sipping coffee as his dad's personal guest after he was plotting with his nephew, not even half an hour ago, to kill him. He was pretty certain there was some higher power that he wronged in a past life that hated his guts."Yeah...that's me!" He said maybe just a little too quickly with his voice cracking before swallowing down the lump in his throat. "Dad...why is he here?"

"Hiccup that's rude!" Stoick scolded before turning to Pitch. "I'm sorry, he sometimes like to look over my files, figures himself a detective, so he's seen your file and some of your work." He then turned to Hiccup. "The mayor has hired Mr. Black to help us with the Dragons. Normally I would disagree but with what happened with Anderson these Dragons must pay for what they've done before someone..." He clapped his shoulder. "More importantly, you, get hurt."

Oh wonderful, not the good father 'I just want to protect you' reason. There was nothing he could say to argue. Now it would be even harder to sneak out, he would have to employ the 'After school study at Astrid's' strategy for the next couple of days."Then it's a pleasure sir to have you on the case." Hiccup sighed holding out his hand for Pitch to shake making sure to keep eye contact.

Pitch stared at his hand before smiling and shaking it. It was an old habit, you can tell a lot just by looking at a person's hand, and it would never hurt to check for weapon. The boy's hand was quite rough for someone his age, as if he spend his time fixing things. A mechanic perhaps? There was also the way he tried his best to keep the eye contact, and how he fidgeted but fixed his figure immediately when he realized it. The Chief's son was used with dealing with carnivores, interesting.

Hiccup pulled his hand back, not liking the way he was being observed, like the way one would look when they were about to pick something apart. He needed space and time so he could formulate a strategy to deal with this new wrinkle. "Well if that's all" He backed away a few steps keeping a smile on. "I'll just be in my room, finishing my homework while you guys talk about police and paid hitman things." He was babbling and he knew it, he was so unprepared for this moment it was far from being funny. He couldn't even hear what he was saying, his blood was pounding in his ears "Bye, nice meeting you sir."

He turned once the back of his foot hit the steps and calmly walked up them closing the door behind him and resting his back on wood. He slid down to the floor his back still against the panel and covered his mouth to stop a choked off sob from coming out. He had dealt with some dangerous individuals in the past but never in his life were they ever this close to dad. There was a professional killer in his house, drinking coffee with his dad, he could easily snap his neck and make Hiccup an orphan. That plus the fact that he going to have to come up with a plan, while this guy was in his house for an undetermined period of time, or Jack and his family would give the Dragons a full on war for braking the deal. Hiccup was pretty certain he was on the verge of a break down. Plus he probably gave himself away, Pitch looked to be the observant type... he used to be in the mafia after all and he was a _**professional**_ killer.

He took a few calming breaths, letting some of his breakdown out as quietly as possible. Pitch only came for files, once he had those he would go. Once he was gone he would call Toothless let him know what happened, call Astrid and tell her as much as he could and set up a 'study date' to keep himself out of Pitch's way. He then wondered if he should call Jack before thinking better of it. Whatever personal vendetta he had would cloud his judgement, also he would back out of the deal if he told him Pitch was in his fucking living room. He would let him know once they got their place in three days time.

Hiccup grabbed his notebook and walked to the window of his room peeking through the blinds. Pitch drove a sleek black Scion, looked expensive along with it being every man's wet dream, yet subtle enough to not draw attention to itself. It had tinted windows, of course, and Hiccup would bet his left leg (Ha!) that when he started the car it would purr so softly he wouldn't even know it was there. License plate, he scowled, hidden. But his knowledge of cars and car parts could get him somewhere, especially since it was a custom job. He could find out where he got it, and the information he put in the registry, including phone number, address and maybe even credit card (though he probably paid cash.)

Though if he was lucky he would leave a number with his dad, contact info or something... maybe he could play the scared son and acquire it. He closed the notebook with all the little detail and shoved it under his pillow before going to his desk and actually starting his homework. Nothing left to do now but wait.

* * *

In The Den, Toothless was being bombarded by questions. Also, those brats that named themselves The Terrible Terrors came again. "Who the fuck let those gremlins in?" He glared at the kids.

Stormfly slapped the back of his head, "Be nice, Meatlug invited them for dinner since not all of us got the privilege of eating in a fancy restaurant."

Toothless bit back his snarks at the mention of Meatlug. "Fine."

Hookfang chuckled and winked knowingly at him. Apparently, his crush on Meatlug wasn't such a secret. "Why don't you tell us more about the meeting?" She smirked.

And so he did.

Hookfang was gazing into nothing with awe when he told them that Hiccup managed to get them a new base. The twins were ecstatic and even those gremlins were excited. "Why are you even excited, you are not one of us." Toothless said dryly."We so are! We helped Boss Lady cleaning up your messes!" The one with snot hanging from his nose puffed his chest proudly. "She even complimented us!""You helped Astrid- never mind." Whatever, Astrid knew what she was doing.

"Sweet, so when do we move out?" Barf asked, his eyes were sparkling with eagerness."Not until three days later, they still need to clean the place up." Toothless answered, which was responded with groans. "Shut up! It's just for three more days! We have been living in this dump for more than that, what's wrong with waiting for a little longer?"

"Toothless is right you know." Meatlug appeared from their makeshift kitchen. Unlike the others, she wasn't wearing what you would call a 'gangster uniform'. Instead, she was wearing a sweater and a plaid skirt, looking very normal and her round glasses gave a good civilian impression. "Just three more days. We can hang on that long. Meanwhile, let's have dinner." She put down a cook pot filled with meat and broth. Meatlug was the expert at scavenging for food (read: stealing from shops without anyone noticing) and was also the group's mother figure.

Toothless reached out for a bowl before Meatlug slapped his hand away. "Ah, ah, you already had your dinner. The Terrors need it more than you." She waved her finger teasingly. Toothless looked so heartbroken that Stormfly couldn't help but bark a round laughter. The man with the ponytail glared at his rival. That was all he could do, glare at her, because Meatlug was here and she wouldn't approve of a fight during dinner. So he sat back and watch as the others ate heartily. Dammit.

* * *

Meanwhile, Hiccup heard the sound of his dad's laugh outside and moved away from his homework to the window trying to hear what they were talking about."I know it's not much, but you are a professional of the trade so surely you could come up with something"

Pitch said something back but Hiccup couldn't make out any words."Well she cares for her city, I'm sure she just wants the problem taken care of and quickly."Again Pitch responded and Hiccup moved a little closer peaking out the window shades."Now why would you need to know something like that?"Know what, what was Pitch asking. Hiccup heard the word 'protect' and felt his stomach do a backflip.

"It's a private school, so that shouldn't be an issue, it's when he's at home and I'm not that I get worried. You know how kids are." Stoick laughed but Pitch did Pitch turned his gaze up making a brief second of eye contact with Hiccup before the boy quickly pulled away from the window. His heart like a humming bird, no way could he have seen him...there was no damn way.

"Yes I know quite well, I have a nephew about his age who is a real terror." He said it loud enough on purpose "Tell your son I look forward to meeting him again."

_You son of a bitch!_ Hiccup gritted his teeth waiting a moment before daring a peek. Man and car were gone with almost no trace of them ever being there in the first let out the breath he didn't know he was holding and with shaky hands he dialed Toothless' number.

* * *

"Hold the fuck up!" Toothless yelled when he felt his old nokia phone vibrated. Stormfly stopped on her track when her sparring partner fished his pocket. It was rare for any Dragons to contact or even know Toothless' number. So for anyone to call him was either in danger or it was their leader. "Yea? You safe Hiccup?" He absent-mindedly twirled his knife. "Oh, your dad didn't find out? Yeah, that's goo-What the fuck?! Who did you say was in your house?!" He gripped his weapon tightly in his hand, as if he was ready to stab something. "But you_ are_ okay, right?"

"I'm fine, I'm fine, don't break the door down" Hiccup smiled feeling a little more at ease but not much. "A bit shaken because I don't know about you, but I did not expect someone dangerous and extremely difficult to find who we just agreed to help kill in my living room drinking coffee" Hiccup's voice cracked a little at the end as he paced his room running a free hand through his hair. "This whole thing is just so messed up. He came here for some files about you guys, the mayor hired him to hunt you. I need to find out what was given, in the meantime look out for a black, custom made, 2012 Scion with a quiet engine and tinted windows. You remember what it looked like when we first pulled up right?"

"Yeah! Yeah..." Toothless disheveled his own hair out of frustration. "I still remember it." He let out a sigh. "We're gonna sniff around the shops. You just... Alright, the twins and those gremlins might not listen to me when I tell them to stay away from you. _Especially_ if I told them the reason why." Oh god, why do those little terrors came in today? "But I'll make sure they stay grounded. You, you stay safe."

It was strange. He was never the type to worry about others, at least, not this much. Maybe it was because The Dragons knew how to take care of themselves, and even though Hiccup was one of them now... The boy didn't have any fighting prowess. He won fights by using his cunning or sheer luck (no matter what he said, Toothless was pretty damn sure the universe liked Hiccup, or else he would have died on their first meeting). He-and perhaps The Dragons as a whole- somehow felt protective over him. If this was how he felt over one incident, he couldn't even fathom how Astrid felt everyday with her in the same school as him. "Be safe okay?"

"Ok" Hiccup sighed a bit of the weight off his shoulders now that he let Toothless know. "I will."

He then stared at his phone wondering if he should worry Astrid this late at night. Exhaustion took over and he decided instead to collapse on the bed and send her a text. 'Study date tomorrow, I'll explain everything. I think someone up there hates me' He waited maybe five minutes before he got a reply.

'I think if someone hates you, you wouldn't have me for a girl friend.'

Hiccup smiled slightly and texted back. 'Astrid you are an angel, I'm happy I have you on my side'

This time it only took two minutes 'Wow no sarcasm, now I'm worried. Is everything ok?'

'Long story and I'm exhausted, either wait till tomorrow or call Toothless if you really need to know. I hate stressing you out over my problems'

This response took a little longer, Hiccup thought maybe that was the end of it until his phone buzzed. 'Your problems are my problems Hiccup, I'll be stressed either way.'

Now why did that take so long to say? Hiccup smiled imagining Astrid on her phone typing something before shaking her head or letting out a frustrated groan before deleting it and starting again. He wished he could see it, not just her face when she got frustrated but also all the messages that she didn't want to send because A) they didn't sound helpful or B) they were cheesy and uncool. Hiccup liked her when she was uncool as much as when she was a HBIC.

In response he figured he should send something dorky or cheesy to ease her mind. He knew she wasn't big on expressing her feelings but embarrassing her was way too much fun.'I love that about you my angel, and I always will. Goodnight'

He imagined Astrid's blushing face and it brought him even more ease of mind than anything else. His phone buzzed after a minute and he looked down at it letting out a chuckle.'I'm going to punch you for that tomorrow you ass!' That was pretty much Astrid-speak for 'I love you too'.

* * *

In the Hofferson's household, Mrs. Hofferson could hear a muffled scream coming from her daughter's room. She was just got home from another meeting with The Mayor, and her heart almost jumped out from her ribcage when she heard Astrid. With the increased crime rate, not to mention the failed infiltration by the cops, her mind panicked and she quickly ran to Astrid's room. "Astrid, are you okay?" She knocked the door when she found it locked.

"I'm okay Mom!" Mrs. Hofferson sighed in relief at her answer. "Oh, and can Hiccup come over tomorrow?" Oh, so that was why! Astrid's mother smiled softly. She would never had thought the Haddock's boy would be the one to catch her daughter's heart. A best friend she could imagine, but finding out that they had been dating for awhile was a shock. Not that Hiccup was a bad kid, far from it even. He was just... Not exactly someone who would attract a girl's attention.

"You wanted to have a date in our house? Astrid, what if he gets bored?" She teased."Mom!" Astrid groaned in . Hofferson chuckled, "Alright, it's fine. The streets aren't safe nowadays anyway..." She mumbled the last bit.

"...I know."

That was the end of their conversation for that night.


End file.
